1-Hydroxybenzotriazole → HCID 9901529, compound

HRID 854102Notes

Reaction equation

HRID 854102 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.[N:33]1[C:42]2[C:37](=[CH:38][C:39]([C:43]([OH:45])=O)=[CH:40][CH:41]=2)[CH:36]=[CH:35][CH:34]=1.C(N(C(C)C)CC)(C)C.[ClH:55].Cl.[NH2:57][CH:58]1[CH:63]2[CH2:64][CH2:65][N:60]([CH2:61][CH2:62]2)[CH2:59]1>CN(C=O)C>[ClH:55].[N:60]12[CH2:65][CH2:64][CH:63]([CH2:62][CH2:61]1)[CH:58]([NH:57][C:43]([C:39]1[CH:38]=[C:37]3[C:42](=[CH:41][CH:40]=1)[N:33]=[CH:34][CH:35]=[CH:36]3)=[O:45])[CH2:59]2

Participants

7

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 825716-Quinolinecarboxylic acidHCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 9901529HCID 9901529, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Firstly, 319 mg (0.99 mmol) of TBTU and 137 mg (1.01 mmol) of HOBt are added to a solution of 182 mg (1.05 mmol) of quinoline-6-carboxylic acid and diisopropylethylamine (620 mg, 4.8 mmol) in 4 mL of DMF at RT, and then 200 mg (1.0 mmol) of 3-aminoquinuclidine dihydrochloride are added. The mixture is stirred at RT for 4 h. For a workup, it is concentrated and taken up in a mixture of chloroform and excess aqueous NaOH. The phases are separated and the aqueous phase is back-extracted several times with chloroform. The combined organic phases are dried over sodium sulfate and concentrated, and the crude product is chromatographed on a silica gel column (mobile, chloroform:methanol: conc. NH3=100:20:4). The resulting product is taken up in THF, excess HCl in diethyl ether is added, and the mixture is concentrated and dried under high vacuum. 136 mg (47% yield) of the hydrochloride are obtained.

Workup

  1. concentrationFor a workup, it is concentrated
  2. additiontaken up in a mixture of chloroform and excess aqueous NaOH
  3. customThe phases are separated
  4. extractionthe aqueous phase is back-extracted several times with chloroform
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. concentrationconcentrated
  7. customthe crude product is chromatographed on a silica gel column (mobile, chloroform:methanol: conc. NH3=100:20:4)
  8. additionexcess HCl in diethyl ether is added
  9. concentrationthe mixture is concentrated
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-33b7aebf138249de812a4baeacce408d
Source dataset
uspto-grants-2007_08
Patent number
US07256288B2

Reaction notes

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